N-(1-methyl-2Phenylethyl)benzamide derivatives

ABSTRACT

A compound of general formula (I): 
     
       
         
         
             
             
         
       
     
     A process for preparing this compound. 
     A fungicidal composition comprising a compound of general formula (I). 
     A method for treating plants by applying a compound of general formula (I) or a composition comprising it.

CROSS REFERENCE TO RELATED APPLICATION(S)

The present application is a 35 U.S.C. §371 national phase conversion ofPCT/EP2006/068717 filed 21 Nov. 2006, which claims priority of EuropeanApplication No. 05356201.3 filed 22 Nov. 2005.

The present invention relates to novel N-(1methyl-2phenylethyl)benzamidederivatives, their process of preparation, their use as fungicides,particularly in the form of fungicidal compositions, and methods for thecontrol of phytopathogenic fungi of plants using these compounds ortheir compositions.

International patent application WO 97/08135 discloses preparation ofacylaminosalicylamides derivatives and their use as fungicide. However,compounds according to the present invention are not disclosed in thatpatent application

It is always of high-interest in the field of agrochemicals to use novelpesticidal compounds with a high efficacy to limit and reduce the riskof appearance of resistant strains in the fungi to be treated.

We have now found a new family of compounds which shows a fungicidalactivity.

Accordingly, the present invention relates to aN-(1methyl-2phenylethyl)benzamide derivative of general formula (I)

-   -   in which:    -   n is 1, 2, 3, 4 or 5;    -   p is 1, 2, 3 or 4;    -   X is the same or different and is a halogen atom, a nitro group,        a cyano group, an amino group, a sulfanyl group, a        pentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxy        group, a formylamino group, a carbamoyl group, a        N-hydroxycarbamoyl group, a carbamate group, a        (hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a        C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a        C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₁-C₈-alkylamino, a        di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkoxy        having 1 to 5 halogen atoms, a C₁-C₈-alkylsulfanyl, a        C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, a        C₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5        halogen atoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy        having 1 to 5 halogen atoms, a C₃-C₈-cycloalkyl, a        C₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonyl having 1 to 5        halogen atoms, a C₁-C₈-alkylcarbamoyl, a        di-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, a        C₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, a        C₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to        5 halogen atoms, a C₁-C₈-alkylcarbonyloxy, a        C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino        having 1 to 5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, a        di-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, a        C₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to        5 halogen atoms, a C₁-C₈-alkylsulphinyl, a        C₁-C₈-halogenoalkylsulphinyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylsulphonyl, a C₁-C₈-halogenoalkyl-sulphonyl having 1        to 5 halogen atoms, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a        (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a        (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a        (benzyloxyimino)-C₁-C₆-alkyl, a benzyloxy, a benzylsulfanyl, a        benzylamino, a phenoxy, a phenylsulfanyl or a phenylamino;    -   R¹ and R² are the same or different and are a hydrogen atom, a        C₁-C₆-alkyl or a C₁-C₆-alkyl-C₃-C₇-cycloalkyl;    -   R³ and R⁴ are the same or different and are a hydrogen atom, a        C₁-C₈-alkyl or a C₁-C₆-alkyl-C₃-C₇-cycloalkyl;    -   R⁵ is a hydrogen atom, a C₁-C₆-alkyl or a C₃-C₇-cycloalkyl;    -   Y is the same or different and is a hydrogen atom, a halogen        atom, a C₁-C₆-alkyl or a C₁-C₆-halogenoalkyl; and    -   Y^(a) is a halogen atom, a C₁-C₈-alkyl or a C₁-C₈-halogenoalkyl;

as well as its salts, N-oxydes, metallic complexes, metalloidiccomplexes and optically active isomers;

with the proviso that compound of general formula (I) is different from:

-   2,3,4,5,6-pentafluoro-N-[2-(2,5-dimethoxyphenyl)-1-methylethyl]-benzamide;-   2,3,4,5,6-pentafluoro-N-[2-(4-methoxyphenyl)-1-methylethyl]-benzamide;-   2,3,4,5,6-pentafluoro-N-[1-methyl-2-(3,4,5-trimethoxyphenyl)ethyl]-benzamide;-   2,3,4,5,6-pentafluoro-N-[1-(phenylmethyl)ethyl-2,2,2-d3]-benzamide;-   2,3,4,5,6-pentafluoro-N-[2-(4-methoxyphenyl)-1-methylethyl]-N-methyl-benzamide;-   2,3,4,5,6-pentafluoro-N-[2-(2-methoxyphenyl)-1-methylethyl]-N-methyl-benzamide;-   2,3,4,5,6-pentafluoro-N-[2-(4-chlorophenyl)-1-methylethyl]-benzamide;-   2-chloro-N-[2-(3-chloro-4-methoxyphenyl)ethyl]-benzamide;-   N-[2-(2-bromophenyl)ethyl]-2-iodobenzamide;-   2-bromo-N-[2-(3,4-dimethoxyphenyl)ethyl]-benzamide;-   2,4-dichloro-N-[1-methyl-2-(3-trifluoromethylphenyl)ethyl]-benzamide;-   2-chloro-N-[2-(3,4-dimethoxyphenyl)ethyl]-benzamide;-   2-chloro-N-[2-(4-chlorophenyl)-1-methyl-ethyl]-benzamide;-   N-[2-(3-chloro-4-methoxyphenyl)ethyl]-2-methylbenzamide;-   N-[2-(3,4-dimethoxyphenyl)ethyl]-2-methylbenzamide;-   2-(2-chloroethyl)-N-[2-(4-methoxyphenyl)ethyl]-benzamide; and-   N-[2-(3-chloro-4-methoxyphenyl)ethyl]-2,6-dimethylbenzamide.

In the context of the present invention:

halogen means fluorine, bromine, chlorine or iodine.

carboxy means —C(═O)OH;

carbonyl means —C(═O)—;

carbamoyl means —C(═O)NH₂;

N-hydroxycarbamoyl means —C(═O)NHOH;

an alkyl group, an alkenyl group, and an alkynyl group as well asmoieties containing these terms, can be linear or branched; and

heteroatom means sulphur, nitrogen or oxygen.

In the context of the present invention, it has also to be understoodthat in the case of di-substituted amino and of di-substituted carbamoylradicals, the two substituents may form together with the nitrogen atombearing them a saturated heterocyclic ring containing 3 to 7 atoms.

Any of the compounds of the present invention can exist in one or moreoptical or chiral isomer forms depending on the number of asymmetriccentres in the compound. The invention thus relates equally to all theoptical isomers and to their racemic or scalemic mixtures (the term“scalemic” denotes a mixture of enantiomers in different proportions),and to the mixtures of all the possible stereoisomers, in allproportions. The diastereoisomers and/or the optical isomers can beseparated according to the methods which are known per se by the manordinary skilled in the art.

Any of the compounds of the present invention can also exist in one ormore geometric isomer forms depending on the number of double bonds inthe compound. The invention thus relates equally to all geometricisomers and to all possible mixtures, in all proportions. The geometricisomers can be separated according to general methods, which are knownper se by the man ordinary skilled in the art.

Any of the compounds of general formula (I) wherein X represents ahydroxy, a sulfanyl group or an amino group may be found in itstautomeric form resulting from the shift of the proton of said hydroxy,sulfanyl or amino group. Such tautomeric forms of such compounds arealso part of the present invention. More generally speaking, alltautomeric forms of compounds of general formula (I) wherein Xrepresents a hydroxy, a sulfanyl group or an amino group, as well as thetautomeric forms of the compounds which can optionally be used asintermediates in the preparation processes, and which will be defined inthe description of these processes, are also part of the presentinvention.

According to the present invention, the phenyl group may be substitutedin any position by (X)_(n), in which X and n are as defined above.Preferably, the present invention relates toN-(1-methyl-2phenylethyl)benzamide derivative of general formula (I) inwhich the different characteristics may be chosen alone or incombination as being:

as regards n, n is 1, 2 or 3. More preferably n is 1 or 2; and

as regards X, X is chosen as being as being a halogen atom, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl or a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl. More preferably X is chosen asbeing a halogen atom or a C₁-C₈-halogenoalkyl having 1 to 5 halogenatoms.

According to the present invention, the carbon atoms of the carboxamidemoiety of the compound of formula (I) are substituted by R¹, R², R³ andR⁴; R′, R², R³ and R⁴ being as defined above. Preferably, the presentinvention also relates to N-(1-methyl-2-phenylethyl)benzamidederivatives of general formula (I) in which the differentcharacteristics may be chosen alone or in combination as being:

as regards R¹ and R², R¹ and R² are chosen, independently of each other,as being a hydrogen atom or a halogen atom;

as regards R³ and R⁴, R³ and R⁴ are chosen, independently of each other,as being a hydrogen atom or C₁-C₆-alkyl. More preferably R³ is chosen asbeing a methyl group and R⁴ is chosen as being a hydrogen atom.

According to the present invention, the nitrogen atom of the carboxamidemoiety of the compound of formula (I) is substituted by R⁵, R⁵ being ahydrogen atom, a C₁-C₆-alkyl or a C₃-C₇-cycloalkyl. Preferably, theC₃-C₇-cycloalkyl is cyclopropyl.

According to the present invention, the ortho-substituted phenyl groupmay be substituted in ortho position by Y^(a) and in any other positionby (Y)_(p), in which Y^(a), Y and p are as defined above. Preferably,the present invention relates to N-(1-methyl-2-phenylethyl)benzamidederivative of general formula (I) in which the different characteristicsmay be chosen alone or in combination as being:

as regards Y^(a), Y^(a) is chosen as being a halogen atom, a C₁-C₆-alkylor a C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms;

as regards p, p is 1 or 2. More preferably p is 1; and

as regards Y, Y is chosen as being a hydrogen atom or a halogen atom.

The present invention also relates to a process for the preparation ofthe compound of general formula (I). Thus, according to a further aspectof the present invention there is provided a process for the preparationof compound of general formula (I) as defined above, which comprisesreacting a 1-alkyl-2phenylethylamine derivative of general formula (II)or one of its salt

-   -   in which R¹, R², R³, R⁴, R⁵, X and n, are as defined above;        with a carboxylic acid derivative of the general formula (III)

-   -   in which:    -   Y^(a), Y and p are as defined above; and

L¹ is a leaving moiety selected from the group consisting of a halogenatom, a hydroxyl group, —OR⁶, and OCOR⁶;

in which:

-   -   R⁶ is selected from the group consisting of a C₁-C₆ alkyl, a        C₁-C₆ haloalkyl, a benzyl, 4-methoxybenzyl, pentafluorophenyl        and a group of formula:

in the presence of a catalyst and, if L¹ is a hydroxyl group, in thepresence of a condensing agent.

The process according to the present invention is conducted in thepresence of a catalyst. Suitable catalyst may be chosen as being4-dimethyl-aminopyridine, 1-hydroxy-benzotriazole or dimethylformamide.

In case L¹ is a hydroxyl group, the process according to the presentinvention is conducted in the presence of condensing agent. Suitablecondensing agent may be chosen as being acid halide former, such asphosgene, phosphorous tribromide, phosphorous trichloride, phosphorouspentachloride, phosphorous trichloride oxide or thionyl chloride;anhydride former, such as ethyl chloroformate, methyl chloroformate,isopropyl chloroformate, isobutyl chloroformate ormethanesulfonyl-chloride; carbodiimides, such asN,N′-dicyclohexylcarbodiimide (DCC) or other customary condensingagents, such as phosphorous pentoxide, polyphosphoric acid,N,N′-carbonyl-diimidazole,2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/tetrachloromethane,4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloridehydrate or bromo-tripyrrolidino-phosphonium-hexafluorophosphate.

When R⁵ is a hydrogen atom, the above mentioned process for thepreparation of compound of general formula (I) may optionally becompleted by a further step according to the following reaction scheme

in which:

-   -   R¹, R², R³, R⁴, X, n, Y^(a), Y and p are as defined above;    -   L² is a leaving group chosen as being a halogen atom, a 4-methyl        phenylsulfonyloxy or a methylsulfonyloxy; and    -   R^(5a) is a C₁-C₆-alkyl group or a C₃-C₇-cycloalkyl; comprising        the reaction of a compound of general formula (Ib) with a        compound of general formula (VI) to provide a compound of        general formula (Ia).

Depending on the definition of R¹, R², R³, R⁴, R⁵, X, and n, aminederivatives of general formula (II) may be prepared by differentprocesses. One example (A) of such a process may be when:

R¹, R², R³, R⁵, X and n are as defined above; and

R⁴ is a hydrogen atom;

then, the amine derivative of general formula (II) may be preparedaccording to a process which comprises:

a first step according to reaction scheme A-1:

-   -   in which R¹, R², R³, R⁵, X and n are as defined above;        comprising the reaction of a compound of general formula (IV)        with an amine of formula R⁵—NH₂ to provide an imine derivative        of general formula (V);

a second step according to scheme A-2

in which R¹, R², R³, R⁵, X and n are as defined above;

comprising the reduction of an imine derivative of general formula (V)by hydrogenation or by an hydride donor, in the same or a different potto provide an amine derivative of general formula (IIa) or one of itssalt. Preferably, the hydride donor is chosen as being metal ormetalloid hydrides such as LiAlH₄, NaBH₄, NaBH₃CN, KBH₄, B₂H₆.

The compound according to the present invention can be preparedaccording to the general processes of preparation described above. Itwill nevertheless be understood that, on the basis of his generalknowledge and of available publications, the skilled worker will be ableto adapt this method according to the specifics of each of thecompounds, which it is desired to synthesise.

On the basis of his general knowledge and of available publications, theskilled worker will also be able to prepare intermediate compound offormula (V) according to the present invention.

The present invention also relates to a fungicidal compositioncomprising an effective amount of an active material of general formula(I). Thus, according to the present invention, there is provided afungicidal composition comprising, as an active ingredient, an effectiveamount of a compound of general formula (I) as defined above and anagriculturally acceptable support, carrier or filler.

In the present specification, the term “support” denotes a natural orsynthetic, organic or inorganic material with which the active materialis combined to make it easier to apply, notably to the parts of theplant. This support is thus generally inert and should be agriculturallyacceptable. The support may be a solid or a liquid. Examples of suitablesupports include clays, natural or synthetic silicates, silica, resins,waxes, solid fertilisers, water, alcohols, in particular butanol,organic solvents, mineral and plant oils and derivatives thereof.Mixtures of such supports may also be used.

The composition may also comprise additional components. In particular,the composition may further comprise a surfactant. The surfactant can bean emulsifier, a dispersing agent or a wetting agent of ionic ornon-ionic type or a mixture of such surfactants. Mention may be made,for example, of polyacrylic acid salts, lignosulphonic acid salts,phenolsulphonic or naphthalenesulphonic acid salts, polycondensates ofethylene oxide with fatty alcohols or with fatty acids or with fattyamines, substituted phenols (in particular alkylphenols or arylphenols),salts of sulphosuccinic acid esters, taurine derivatives (in particularalkyl taurates), phosphoric esters of polyoxyethylated alcohols orphenols, fatty acid esters of polyols, and derivatives of the abovecompounds containing sulphate, sulphonate and phosphate functions. Thepresence of at least one surfactant is generally essential when theactive material and/or the inert support are water-insoluble and whenthe vector agent for the application is water. Preferably, surfactantcontent may be comprised between 5% and 40% by weight of thecomposition.

Optionally, additional components may also be included, e.g. protectivecolloids, adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active materialscan be combined with any solid or liquid additive, which complies withthe usual formulation techniques.

In general, the composition according to the invention may contain from0.05 to 99% (by weight) of active material, preferably 10 to 70% byweight.

Compositions according to the present invention can be used in variousforms such as aerosol dispenser, capsule suspension, cold foggingconcentrate, dustable powder, emulsifiable concentrate, emulsion oil inwater, emulsion water in oil, encapsulated granule, fine granule,flowable concentrate for seed treatment, gas (under pressure), gasgenerating product, granule, hot fogging concentrate, macrogranule,microgranule, oil dispersible powder, oil miscible flowable concentrate,oil miscible liquid, paste, plant rodlet, powder for dry seed treatment,seed coated with a pesticide, soluble concentrate, soluble powder,solution for seed treatment, suspension concentrate (flowableconcentrate), ultra low volume (ulv) liquid, ultra low volume (ulv)suspension, water dispersible granules or tablets, water dispersiblepowder for slurry treatment, water soluble granules or tablets, watersoluble powder for seed treatment and wettable powder.

These compositions include not only compositions which are ready to beapplied to the plant or seed to be treated by means of a suitabledevice, such as a spraying or dusting device, but also concentratedcommercial compositions which must be diluted before application to thecrop.

The compounds of the invention can also be mixed with one or moreinsecticides, fungicides, bactericides, attractant acaricides orpheromones or other compounds with biological activity. The mixturesthus obtained have a broadened spectrum of activity. The mixtures withother fungicides are particularly advantageous. Examples of suitablefungicide mixing partners may be selected in the following lists:

1) a compound capable to inhibit the nucleic acid synthesis likebenalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon,dimethirimol, ethirimol, furalaxyl, hymexazol, mefenoxam, metalaxyl,metalaxyl-M, ofurace, oxadixyl, oxolinic acid;

2) a compound capable to inhibit the mitosis and cell division likebenomyl, carbendazim, diethofencarb, ethaboxam, fuberidazole,pencycuron, thiabendazole thiophanate-methyl, zoxamide;

3) a compound capable to inhibit the respiration for example

as CI-respiration inhibitor like diflumetorim;

as CII-respiration inhibitor like boscalid, carboxin, fenfuram,flutolanil, furametpyr, furmecyclox, mepronil, oxycarboxine,penthiopyrad, thifluzamide;

as CIII-respiration inhibitor like amisulbrom, azoxystrobin, cyazofamid,dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin,kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin,pyraclostrobin, trifloxystrobin;

4) a compound capable of to act as an uncoupler like dinocap, fluazinam,meptyldinocap;

5) a compound capable to inhibit ATP production like fentin acetate,fentin chloride, fentin hydroxide, silthiofam;

6) a compound capable to inhibit AA and protein biosynthesis likeandoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycinhydrochloride hydrate, mepanipyrim, pyrimethanil;

7) a compound capable to inhibit the signal transduction likefenpiclonil, fludioxonil, quinoxyfen;

8) a compound capable to inhibit lipid and membrane synthesis likebiphenyl, chlozolinate, edifenphos, etridiazole, iodocarb, iprobenfos,iprodione, isoprothiolane, procymidone, propamocarb, propamocarbhydrochloride, pyrazophos, tolclofos-methyl, vinclozolin;

9) a compound capable to inhibit ergosterol biosynthesis like aldimorph,azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole,difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorphacetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole,fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol,flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole,imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole,myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol,pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole,pyributicarb, pyrifenox, simeconazole, spiroxamine, tebuconazole,terbinafine, tetraconazole, triadimefon, triadimenol, tridemorph,triflumizole, triforine, triticonazole, uniconazole, viniconazole,voriconazole;

10) a compound capable to inhibit cell wall synthesis likebenthiavalicarb, bialaphos, dimethomorph, flumorph, iprovalicarb,mandipropamid, polyoxins, polyoxorim, validamycin A;

11) a compound capable to inhibit melanine biosynthesis likecarpropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole;

12) a compound capable to induce a host defence likeacibenzolar-S-methyl, probenazole, tiadinil;

13) a compound capable to have a multisite action like Bordeaux mixture,captafol, captan, chlorothalonil, copper naphthenate, copper oxide,copper oxychloride, copper preparations such as copper hydroxide, coppersulphate, dichlofluanid, dithianon, dodine, dodine free base, ferbam,fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine,iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb,maneb, metiram, metiram zinc, oxine-copper, propineb, sulphur andsulphur preparations including calcium polysulphide, thiram,tolylfluanid, zineb, ziram;

14) a compound selected in the following list:(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide,(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol,1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl-1H-imidazole-1-carboxylate,2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine,2-butoxy-6-iodo-3-propyl-4H-chromen-4-one,2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)nicotinamide,2-phenylphenol and salts, 3,4,5-trichloropyridine-2,6-dicarbonitrile,3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide,3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1R)-1,2,2-trimethylpropyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine,5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,8-hydroxyquinoline sulfate, benthiazole, bethoxazin, capsimycin,carvone, chinomethionat, cufraneb, cyflufenamid, cymoxanil, dazomet,debacarb, dichlorophen, diclomezine, dicloran, difenzoquat, difenzoquatmethylsulphate, diphenylamine, ferimzone, flumetover, fluopicolide,fluoroimide, flusulfamide, fosetyl-aluminium, fosetyl-calcium,fosetyl-sodium, hexachlorobenzene, irumamycin, isotianil,methasulfocarb, methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}thio)methyl]phenyl}-3-methoxyacrylate,methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,methyl isothiocyanate, metrafenone, mildiomycin,N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide,N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N<-(methylsulfonyl)valinamide,N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-{2-[1,1′-bi(cyclopropyl)-2-yl]phenyl}-3-(difluoromethyl)-,1-methyl-1H-pyrazole-4-carboxamide,N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide,natamycin,N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide,N-ethyl-N-methyl-N′-{2-methyl-5-(difluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide,nickel dimethyldithiocarbamate, nitrothal-isopropyl,O-{1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl}1H-imidazole-1-carbothioate,octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts,phosphorous acid and its salts, piperalin, propamocarb fosetylate,propanosine-sodium, proquinazid, pyribencarb, pyrroInitrine, quintozene,tecloftalam, tecnazene, triazoxide, trichlamide, valiphenal, zarilamid.

The composition according to the invention comprising a mixture of acompound of formula (I) with a bactericide compound may also beparticularly advantageous. Examples of suitable bactericide mixingpartners may be selected in the following list: bronopol, dichlorophen,nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone,furancarboxylic acid, oxytetracycline, probenazole, streptomycin,tecloftalam, copper sulphate and other copper preparations.

The fungicidal compositions of the present invention can be used tocuratively or preventively control the phytopathogenic fungi of crops.Thus, according to a further aspect of the present invention, there isprovided a method for curatively or preventively controlling thephytopathogenic fungi of crops characterised in that a fungicidalcomposition as hereinbefore defined is applied to the seed, the plantand/or to the fruit of the plant or to the soil in which the plant isgrowing or in which it is desired to grow.

The composition as used against phytopathogenic fungi of crops comprisesan effective and non-phytotoxic amount of an active material of generalformula (I).

The expression “effective and non-phytotoxic amount” means an amount ofcomposition according to the invention which is sufficient to control ordestroy the fungi present or liable to appear on the crops, and whichdoes not entail any appreciable symptom of phytotoxicity for the saidcrops. Such an amount can vary within a wide range depending on thefungus to be controlled, the type of crop, the climatic conditions andthe compounds included in the fungicidal composition according to theinvention.

This amount can be determined by systematic field trials, which arewithin the capabilities of a person skilled in the art.

The method of treatment according to the present invention is useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.This method of treatment can also be useful to treat roots. The methodof treatment according to the present invention can also be useful totreat the overground parts of the plant such as trunks, stems or stalks,leaves, flowers and fruits of the concerned plant.

Among the plants that can be protected by the method according to thepresent invention, mention may be made of cotton; flax; vine; fruit orvegetable crops such as Rosaceae sp. (for instance pip fruit such asapples and pears, but also stone fruit such as apricots, almonds andpeaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp.,Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp.,Actimidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana treesand plantins), Rubiaceae sp., Theaceae sp., Sterculiceae sp., Rutaceaesp. (for instance lemons, oranges and grapefruit); Solanaceae sp. (forinstance tomatoes), Liliaceae sp., Asteraceae sp. (for instancelettuces), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp.,Cucurbitaceae sp., Papilionaceae sp. (for instance peas), Rosaceae sp.(for instance strawberries); major crops such as Graminae sp. (forinstance maize, lawn or cereals such as wheat, rice, barley andtriticale), Asteraceae sp. (for instance sunflower), Cruciferae sp. (forinstance colza), Fabacae sp. (for instance peanuts), Papilionaceae sp.(for instance soybean), Solanaceae sp. (for instance potatoes),Chenopodiaceae sp. (for instance beetroots); horticultural and forestcrops; as well as genetically modified homologues of these crops.

Among the diseases of plants or crops that can be controlled by themethod according to the present invention, mention may be made of:

Powdery mildew diseases such as:

Blumeria diseases, caused for example by Blumeria graminis;

Podosphaera diseases, caused for example by Podosphaera leucotricha;

Sphaerotheca diseases, caused for example by Sphaerotheca fuliginea;

Uncinula diseases, caused for example by Uncinula necator;

Rust diseases such as:

Gymnosporangium diseases, caused for example by Gymnosporangium sabinae;

Hemileia diseases, caused for example by Hemileia vastatrix;

Phakopsora diseases, caused for example by Phakopsora pachyrhizi orPhakopsora meibomiae;

Puccinia diseases, caused for example by Puccinia recondita;

Uromyces diseases, caused for example by Uromyces appendiculatus;

Oomycete diseases such as:

Bremia diseases, caused for example by Bremia lactucae;

Peronospora diseases, caused for example by Peronospora pisi or P.brassicae;

Phytophthora diseases, caused for example by Phytophthora infestans;

Plasmopara diseases, caused for example by Plasmopara viticola;

Pseudoperonospora diseases, caused for example by Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Pythium diseases, caused for example by Pythium ultimum; Leafspot, leafblotch and leaf blight diseases such as:

Alternaria diseases, caused for example by Alternaria solani;

Cercospora diseases, caused for example by Cercospora beticola;

Cladiosporum diseases, caused for example by Cladiosporium cucumerinum;

Cochliobolus diseases, caused for example by Cochliobolus sativus;

Colletotrichum diseases, caused for example by Colletotrichumlindemuthanium;

Cycloconium diseases, caused for example by Cycloconium oleaginum;

Diaporthe diseases, caused for example by Diaporthe citri;

Elsinoe diseases, caused for example by Elsinoe fawcettii;

Gloeosporium diseases, caused for example by Gloeosporium laeticolor;

Glomerella diseases, caused for example by Glomerella cingulata;

Guignardia diseases, caused for example by Guignardia bidwelli;

Leptosphaeria diseases, caused for example by Leptosphaeria maculans;Leptosphaeria nodorum;

Magnaporthe diseases, caused for example by Magnaporthe grisea;

Mycosphaerella diseases, caused for example by Mycosphaerellagraminicola; Mycosphaerella arachidicola; Mycosphaerella fjiensis;

Phaeosphaeria diseases, caused for example by Phaeosphaeria nodorum;

Pyrenophora diseases, caused for example by Pyrenophora teres;

Ramularia diseases, caused for example by Ramularia collo-cygni;

Rhynchosporium diseases, caused for example by Rhynchosporium secalis;

Septoria diseases, caused for example by Septoria apii or Septorialycopercisi;

Typhula diseases, caused for example by Typhula incarnata;

Venturia diseases, caused for example by Venturia inaequalis;

Root and stem diseases such as:

Corticium diseases, caused for example by Corticium graminearum;

Fusarium diseases, caused for example by Fusarium oxysporum;

Gaeumannomyces diseases, caused for example by Gaeumannomyces graminis;

Rhizoctonia diseases, caused for example by Rhizoctonia solani;

Tapesia diseases, caused for example by Tapesia acuformis;

Thielaviopsis diseases, caused for example by Thielaviopsis basicola;

Ear and panicle diseases such as:

Alternaria diseases, caused for example by Alternaria spp.;

Aspergillus diseases, caused for example by Aspergillus flavus;

Cladosporium diseases, caused for example by Cladosporium spp.;

Claviceps diseases, caused for example by Claviceps purpurea;

Fusarium diseases, caused for example by Fusarium culmorum;

Gibberella diseases, caused for example by Gibberella zeae;

Monographella diseases, caused for example by Monographella nivalis;

Smut and bunt diseases such as:

Sphacelotheca diseases, caused for example by Sphacelotheca reiliana;

Tilletia diseases, caused for example by Tilletia caries;

Urocystis diseases, caused for example by Urocystis occulta;

Ustilago diseases, caused for example by Ustilago nuda;

Fruit rot and mould diseases such as:

Aspergillus diseases, caused for example by Aspergillus flavus;

Botrytis diseases, caused for example by Botrytis cinerea;

Penicillium diseases, caused for example by Penicillium expansum;

Sclerotinia diseases, caused for example by Sclerotinia sclerotiorum;

Verticilium diseases, caused for example by Verticilium alboatrum;

Seed and soilborne decay, mould, wilt, rot and damping-off diseases:

Fusarium diseases, caused for example by Fusarium culmorum;

Phytophthora diseases, caused for example by Phytophthora cactorum;

Pythium diseases, caused for example by Pythium ultimum;

Rhizoctonia diseases, caused for example by Rhizoctonia solani;

Sclerotium diseases, caused for example by Sclerotium rolfsii;

Microdochium diseases, caused for example by Microdochium nivale;

Canker, broom and dieback diseases such as:

Nectria diseases, caused for example by Nectria galligena;

Blight diseases such as:

Monilinia diseases, caused for example by Monilinia laxa;

Leaf blister or leaf curl diseases such as:

Taphrina diseases, caused for example by Taphrina deformans;

Decline diseases of wooden plants such as:

Esca diseases, caused for example by Phaemoniella clamydospora;

Diseases of flowers and Seeds such as:

Botrytis diseases, caused for example by Botrytis cinerea;

Diseases of tubers such as:

Rhizoctonia diseases, caused for example by Rhizoctonia solani.

The fungicide composition according to the present invention may also beused against fungal diseases liable to grow on or inside timber. Theterm “timber” means all types of species of wood, and all types ofworking of this wood intended for construction, for example solid wood,high-density wood, laminated wood, and plywood. The method for treatingtimber according to the invention mainly consists in contacting one ormore compounds of the present invention, or a composition according tothe invention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

The dose of active material usually applied in the treatment accordingto the present invention is generally and advantageously between 10 and800 g/ha, preferably between 50 and 300 g/ha for applications in foliartreatment. The dose of active substance applied is generally andadvantageously between 2 and 200 g per 100 kg of seed, preferablybetween 3 and 150 g per 100 kg of seed in the case of seed treatment. Itis clearly understood that the doses indicated above are given asillustrative examples of the invention. A person skilled in the art willknow how to adapt the application doses according to the nature of thecrop to be treated.

The fungicidal composition according to the present invention may alsobe used in the treatment of genetically modified organisms with thecompounds according to the invention or the agrochemical compositionsaccording to the invention. Genetically modified plants are plants intowhose genome a heterologous gene encoding a protein of interest has beenstably integrated. The expression “heterologous gene encoding a proteinof interest” essentially means genes which give the transformed plantnew agronomic properties, or genes for improving the agronomic qualityof the transformed plant.

The compositions according to the present invention may also be used forthe preparation of composition useful to curatively or preventivelytreat human and animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp., for example Aspergillus fumigatus.

The aspects of the present invention will now be illustrated withreference to the following tables of compounds and examples. Thefollowing Table illustrates in a non-limiting manner examples offungicidal compounds according to the present invention. In thefollowing Examples, M+1 (or M−1) means the molecular ion peak, plus orminus 1 a.m.u. (atomic mass units) respectively, as observed in massspectroscopy and M (ApcI+) means the molecular ion peak as it was foundvia positive atmospheric pressure chemical ionisation in massspectroscopy.

Compound R¹ R² R³ R⁴ R⁵ X¹ X² X³ X⁴ X⁵ Y¹ Y² Y³ Y⁴ Y^(a) (M + 1) 1 H HMe H H H H Cl H H H H H H CF3 342 2 H H Me H Cyclopropyl H H Cl H H H HH H CF3 382 3 H H Me H Cyclopropyl H H Cl H H H H H H Br 392 4 H H Me HCyclopropyl H H Cl H H H H H H I 440 5 H H Me H Cyclopropyl H H Cl H H HH H H Cl 348 6 H H Me H Cyclopropyl H H Cl H H H H H H Me 328 7 H H Me HCyclopropyl H H Cl H H H H H H CHF2 363 8 H H Me H H H H Cl H H H H H ClCl 342 9 H H Me H H H H Cl H H H H H H Br 352 10 H H Me H H H H Cl H H HH H H CHF2 324

EXAMPLES OF PROCESS FOR THE PREPARATION OF THE COMPOUND OF GENERALFORMULA (I) Preparation of2,6-dichloro-N-[2-(4-chlorophenyl)-1-methylethyl]benzamide, (Compound 8)

100 mg of 1-(4-chlorophenyl)propan-2-amine hydrochloride (0.728 mmol)and 0.10 ml of triethylamine (0.728 mmol) are diluted in 3 ml ofdichloromethane at room temperature, 152 mg of 2,6-dichlorobenzoylchloride (0.728 mmol) are added to the reaction mixture. After 24 hoursof stirring, 20 ml of DCM an 10 ml of saturated solution of ammoniumchloride are added to the reaction mixture.

After separation, the organic phase is washed with 10 ml of a saturatedsolution of sodium bicarbonate.

After separation over magnesium sulphate, filtration and concentrationin vacuo, 0.24 g of essentially pure2,6-dichloro-N-[2-(4-chlorophenyl)-1-methylethyl]benzamide are obtained(yield=93%).

[M+1]=342

Preparation ofN-[2-(4-chlorophenyl)-1-methylethyl]-N-cyclopropyl-2-(difluoromethyl)benzamide(Compound 7) Preparation ofN-[2-(4-chlorophenyl)-1-methylethyl]cyclopropanamine hydrochloride

Under argon are mixed, in 150 ml of methanol, 10.1 g of cyclopropylamine(0.177 mol) and 12.6 ml of acetic acid (0.221 mol). 15.0 g of1-(4-chlorophenyl)acetone (0.088 mol) and 15 g of 3 Å molecular sievesare then added. The reaction mixture is refluxed for 3 hours. Aftercooling to room temperature, 8.34 g of sodium cyanoborohydride (0.13mol) are added to the reaction mixture which is refluxed again for 3hours. After one night at room temperature, 3 g of cyanoborhydride(0.048 mol) and 8 ml of acetic acid (0.126 mol) are added to thereaction mixture which is refluxed for three hours. After cooling toroom temperature, filtration over celite and concentration in vacuo, 250ml of dichloromethane and 400 ml of NaOH 1M are added to the reactionmixture.

After separation, the aqueous phase is extracted with 250 ml ofdichloromethane, the combined organic phases are washed with 1550 ml ofwater and 200 ml of brine.

After drying over magnesium sulphate, filtration and concentration, thecrude amine is precipitated with HCl 2M in ether to yield to 19.06 g ofN-[2-(4-chlorophenyl)-1-methylethyl]cyclopropanamine hydrochloride(yield=88%).

[M+1-HCl]=210.

Preparation ofN-[2-(4-chlorophenyl)-1-methylethyl]-N-cyclopropyl-2-(difluoromethyl)benzamide

300 mg of N-[2-(4-chlorophenyl)-1-methylethyl]cyclopropanaminehydrochloride (1.218 mmol), 220 mg of 2-(difluoromethyl)benzoic acid(1.28 mmol), 16 mg of 1-hydroxybenzotriazole (0.12 mmol), 256 mg of1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.34 mmol)and 0.171 ml of TEA (1.22 mmol) are refluxed in 10 ml of dichloromethanefor one hour. After 48 hours at room temperature, the reaction isquenched with 5 ml of HCl 0.5M.

After separation, the organic phase is washed with 5 ml of water and 5ml of a saturated solution of sodium bicarbonate, dried over magnesiumsulphate, filtered and concentrated in vacuo. The crude product isflash-chromatographed on silica with heptane/EtOAc to yield to 149 mg ofN-[2-(4-chlorophenyl)-1-methylethyl]-N-cyclopropyl-2-(difluoromethyl)benzamide(yield=37%).

[M+1]=363.

EXAMPLES OF BIOLOGICAL ACTIVITY OF THE COMPOUND OF GENERAL FORMULA (I)Example A In Vivo Test on Alternaria brassicae (Leaf Spot of Crucifers)

The active ingredients tested are prepared by homogenisation in amixture of acetone/tween/DMSO, then diluted with water to obtain thedesired active material concentration.

Radish plants (Pernot variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 18-20° C., are treated at thecotyledon stage by spraying with the active ingredient prepared asdescribed above.

Plants, used as controls, are treated with the mixture ofacetone/tween/DMSO/water not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Alternaria brassicae spores (40,000 spores percm³). The spores are collected from a 12 to 13 days-old culture.

The contaminated radish plants are incubated for 6-7 days at about 18°C., under a humid atmosphere.

Grading is carried out 6 to 7 days after the contamination, incomparison with the control plants.

Under these conditions, good (at least 70%) or total protection isobserved at a dose of 500 ppm with the following compounds: 1, 9 and 10.

Example B In Vivo Test on Pyrenophora teres (Barley Net Blotch)

The active ingredients tested are prepared by homogenisation in amixture of acetone/tween/DMSO, then diluted with water to obtain thedesired active material concentration.

Barley plants (Express variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the active ingredient prepared asdescribed above. Plants, used as controls, are treated with the mixtureof acetone/tween/DMSO/water not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Pyrenophora teres spores (12,000 spores per ml).The spores are collected from a 12-day-old culture. The contaminatedbarley plants are incubated for 24 hours at about 20° C. and at 100%relative humidity, and then for 12 days at 80% relative humidity.

Grading is carried out 12 days after the contamination, in comparisonwith the control plants.

Under these conditions, good (at least 70%) or total protection isobserved at a dose of 500 ppm with the following compound: 1.

Example C In Vivo Test on Mycosphaerella graminicola (Wheat Leaf Spot)

The active ingredients tested are prepared by homogenisation in amixture of acetone/tween/DMSO, then diluted with water to obtain thedesired active material concentration.

Wheat plants (Scipion variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the active ingredient prepared asdescribed above.

Plants, used as controls, are treated with the mixture ofacetone/tween/DMSO/water not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Mycosphaerella graminicola spores (500 000 sporesper ml). The spores are collected from a 7-day-old culture. Thecontaminated wheat plants are incubated for 72 hours at 18° C. and at100% relative humidity, and then for 21 to 28 days at 90% relativehumidity.

Grading (% of efficacy) is carried out 21 to 28 days after thecontamination, in comparison with the control plants.

Under these conditions, good (at least 70%) or total protection isobserved at a dose of 500 ppm with the following compounds: 1, 9 and 10.

1. A compound derivative of formula (I)

in which: n is 1, 2, or 3; p is 1 or 2; each X is the is independentlyselected from the group consisting of a halogen atom, a nitro group, acyano group, an amino group, a sulfanyl group, a pentafluoro-λ⁶-sulfanylgroup, a formyl group, a formyloxy group, a formylamino group, acarbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₁-C₈-alkylamino, a di-C₁-C₈-alkylamino, a a C₁-C₈-halogenoalkoxy having1 to 5 halogen atoms, a C₁-C₈-alkylsulfanyl, aC₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, aC₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogenatoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5halogen atoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈alkylsulfenyl, a C₁-C₈-halogenoalkylsulfenyl having 1 to 5 halogenatoms, a C₁-C₈-alkylsulfinyl, a C₁-C₈-halogenoalkylsulfinyl having 1 to5 halogen atoms, a C₁-C₈-alylsulfonyl, C₁-C₈-halogenoalkylsulfonylhaving 1 to 5 halogen atoms, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a (benzyloxyimino)-C₁-C₆-alkyl, abenzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanyland a phenylamino; R¹ and R² are independently selected from the groupconsisting of a hydrogen atom, a C₁-C₆-alkyl and aC₁-C₆-alkyl-C₃-C₇cycloalkyl; R³ and R⁴ are independently selected fromthe group consisting of a hydrogen atom, a C₁-C₈-alkyl and aC₁-C₆-alkyl-C₃-C₇-cycloalkyl; R⁵ is selected from the group consistingof a hydrogen atom, a C₁-C₆-alkyl or and a C₃-C₇-cycloalkyl; each Y isindependently selected from the group consisting of a hydrogen atom, ahalogen atom, a C₁-C₆-alkyl and a C₁-C₆-halogenoalkyl; and Y^(a) isselected from the group consisting of a halogen atom, a C₁-C₈-alkyl anda C₁-C₈-halogenoalkyl; as well as its salts, N-oxides, metalliccomplexes, metalloidic complexes and optically active isomers; with theproviso that compound of general formula (I) is different from:N-[2-(2-bromophenyl)ethyl]-2-iodobenzamide;2,4-dichloro-N-[1-methyl-2-(3-trifluoromethylphenyl)ethyl]-benzamide;and 2-chloro-N-[2-(4-chlorophenyl)-1-methyl-ethyl]-benzamide.
 2. Thecompound according of claim 1, wherein each X is independently selectedfrom the group consisting of a halogen atom, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl and a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl.
 3. The compound of claim 1, whereinR¹ and R² are independently selected from the group consisting of ahydrogen atom and a halogen atom.
 4. The compound according of claim 1,wherein R³ and R⁴ are independently selected from the group consistingof a hydrogen atom and C₁-C₆-alkyl.
 5. The compound of claim 1, whereinY^(a) is being selected from the group consisting of a halogen atom, aC₁-C₆-alkyl and a C₁-C₆-halogenoalkyl having 1 to 5 halogen atoms. 6.The compound of claim 1, wherein each Y is independently selected fromthe group consisting of a hydrogen atom and a halogen atom.
 7. A processfor the preparation of a compound of formula (I), which comprises a1-alkyl-2-phenylethylamine derivative of formula (II) or one of itssalts

in which: n is 1, 2, or 3; each X is independently selected from thegroup consisting of a halogen atom, a nitro group, a cyano group, anamino group, a sulfanyl group, a pentafluoro-λ⁶-sulfanyl group, a formylgroup, a formyloxy group, a formylamino group, a carbamoyl group, aN-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms, a C₇-C₈-alkenyl, a C₂-C₈-alkynyl, aC₁-C₈-alkylamino, a di-C₁-C₈-alkylamino, a C₁-C₈-halogenoalkoxy having 1to 5 halogen atoms, a C₁-C₈-alkylsulfanyl, a C₁-C₈ halogenoalkylsulfanylhaving 1 to 5 halogen atoms, a C₇-C₈-alkenyloxy, aC₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, aC₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5 halogenatoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₃-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₃-alkyloxycarbamoyl aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoallylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈-alkylsulfenyl, a C₁-C₈-halogenoalkylsulfenyl having 1 to 5 halogenatoms, a C₁-C₈-alkylsulfinyl, a C₁-C₃-halogenoalkylsulfinyl having 1 to5 halogen atoms, a C₁-C₈-alkylsulfonyl, a C₁-C₈-halogenoalkylsulfonylhaving 1 to 5 halogen atoms, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkynyloxyimino-C₁-C₆-alkyl, a (benzyloxyimino)-C₁-C₆-alkyl, abenzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanyland a phenylamino; R¹ and R² are independently selected from the groupconsisting of a hydrogen atom, a C₁-C₆-alkyl and aC₁-C₆-alkyl-C₃-C₇-cycloalkyl; R³ and R⁴ are independently selected fromthe group consisting of a hydrogen atom, a C₁-C₆-alkyl and aC₁-C₆-alkyl-C₃-C₇-cycloalkyl; and R⁵ is selected from the groupconsisting of a hydrogen atom, a C₁-C₆-alkyl and a C₃-C₇-cycloalkyl;with a carboxylic acid derivative of formula (III)

in which: p is 1 or 2; each Y is independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a C₁-C₆-alkyl and aC₁-C₆-halogenoalkyl; Y^(a) is selected from the group consisting of ahalogen atom, a C₁-C₆-alkyl and a C₁-C₆-halogenoalkyl; and L¹ is aleaving moiety selected from the group consisting of a halogen atom, ahydroxyl group, —OR⁶, and —OCOR⁶; in which: R⁶ is selected from thegroup consisting of a C₁-C₆ alkyl, a C₁-C₆ haloalkyl, a benzyl,4-methoxybenzyl, pentafluorophenyl and a group of formula:

in the presence of a catalyst and, if L¹ is a hydroxyl group, in thepresence of a condensing agent.
 8. The process of claim 7, wherein R⁵ isa hydrogen atom and that the process further comprises completing by afurther step according to the following reaction scheme:

in which: L² is a leaving moiety selected from the group consisting of ahalogen atom, a 4-methyl phenylsulfonyloxy and a methylsulfonyloxy; andR^(5a) is selected from the group consisting of a C₁-C₆-alkyl group orand a C₃-C₇-cycloalkyl; wherein said further step comprises reacting acompound of formula (Ib) with a compound of formula (VI) to provide acompound of formula (Ia).
 9. A fungicide composition comprising aneffective amount of a compound according to claim 1 and anagriculturally acceptable support.
 10. A method for combating thephytopathogenic fungi of plants comprising applying an effective andnon-phytotoxic amount of the composition of claim 9 to the plant seedsor to the plant leaves and/or to the fruits of the plants or to the soilin which the plants are growing or in which it is desired to grow them.11. The compound of claim 1 wherein: each X is independently selectedfrom the group consisting of a halogen atom, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈ alkyl, a C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl and a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl; R¹ and R² are independentlyselected from the group consisting of a hydrogen atom and a halogenatom; R³ and R⁴ are independently selected from the group consisting ofa hydrogen atom and C₁-C₆-alkyl; Y^(a) is selected from the groupconsisting of a halogen atom, a C₁-C₆-alkyl and a C₁-C₆-halogenoalkylhaving 1 to 5 halogen atoms; and each Y is independently selected fromthe group consisting of a hydrogen atom and a halogen atom.
 12. Afungicide composition comprising an effective amount of a compoundaccording to claim 11 and an agriculturally acceptable support.
 13. Amethod for combating the phytopathogenic fungi of plants comprisingapplying an effective and non-phytotoxic amount of the composition ofclaim 12 to the plant seeds or to the plant leaves and/or to the fruitsof the plants or to the soil in which the plants are growing or in whichit is desired to grow them.
 14. The compound of claim 11 wherein saidcompound is selected from the group consisting of:


15. A fungicide composition comprising an effective amount of a compoundaccording to claim 14 and an agriculturally acceptable support.
 16. Amethod for combating the phytopathogenic fungi of plants comprisingapplying an effective and non-phytotoxic amount of the composition ofclaim 15 to the plant seeds or to the plant leaves and/or to the fruitsof the plants or to the soil in which the plants are growing or in whichit is desired to grow them.